A three-time World Series champion who twice bested the Cardinals on his way to the title, Jon Lester took an unexpected detour into a Cardinals jersey along the route to his 200th win.
Lester, 38, has decided it also will be his last win.
The lefty confirmed his retirement Wednesday, closing a remarkably durable career that spans 16 years, 452 major-league games, championships with the Red Sox and Cubs, and those four wins with the Cardinals after a deadline trade in 2021 to give him a tidy 200-117 record at the end.
“It’s kind of run its course,” Lester told ESPN baseball writer Jesse Rogers in a story published Wednesday. “It’s getting harder for me physically. The little things that come up throughout the year turned into bigger things that hinder your performance. I’d like to think I’m a halfway decent self-evaluator. I don’t want someone else telling me I can’t do this anymore.”
One of the final trades approved before the deadline last July was the Cardinals’ agreement to send outfielder Lane Thomas to Washington for the veteran lefty Lester. The trade surprised Lester after a career heightened by competing against the Cardinals, but the 6-foot-4 lefty pointed out soon after that he did not have the protection of a no-trade clause to choose a destination.
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He said the deal gave him a chance at reinvention.
A new start
Working with pitching coach Mike Maddux and alongside Adam Wainwright and watching catcher Yadier Molina, Lester changed his pitch sequencing, used his changeup differently, and put the Cardinals’ defense to work more often with his sinker. Lester cut his flyball rate down — and his ERA followed. In 16 starts for the Nationals, Lester was 3-5 with a 5.02 ERA. After the deadline, Lester made 12 starts for the Cardinals and went 4-1 with a 4.36 ERA.
He and fellow lefty J.A. Happ helped the Cardinals out of an innings crisis and into a playoff berth.
“He’s like John Wayne,” then-Cardinals manager Mike Shildt said of Lester. “Got that true grit.”
During the 17-game winning streak that made the postseason possible, Lester claimed his 200th win in Milwaukee on Sept. 20. Lester allowed two runs (both on homers) and three hits in six innings as the Cardinals won 5-2. That was the ninth consecutive win of a streak that would shatter the previous club record of 14.
“Playing with ‘Waino’ and Yadi was awesome,” Lester told ESPN. “It was a cool experience to play for that organization. You learn to understand why they’re so successful every year.”
Lester became the third active pitcher with 200 wins, joining Justin Verlander and Zack Greinke. With Lester’s retirement, New York Mets righthander and Mizzou great Max Scherzer becomes the next active pitcher nearing 200; the three-time Cy Young winner has 190. Behind him are Clayton Kershaw (185) and Cardinals veteran Wainwright (184).
Boston’s second-round pick in the 2002 draft, Lester debuted four years later and made 15 starts as a rookie. Late in that season he was diagnosed with lymphoma and underwent chemotherapy. He rejoined the Red Sox and their rotation midway through the 2007 season.
For the next 14 seasons he was a metronome of reliability. Of his 452 career appearances, 451 were starts. He had 12 seasons of at least 30 starts, including seven consecutive early in his career. Lester won World Series titles with the Red Sox in 2007 and 2013, when he went 2-0 with a 0.59 ERA against the Cardinals.
Before the 2015 season, he signed with the Chicago Cubs — the blockbuster signing on the north side that legitimized and accelerated the construction of a championship club.
Lester went 19-5 with a 2.44 ERA in 2016 as the Cubs won the National League Central Division title and rallied against Cleveland in Game 7 to win the club’s first World Series since 1908.
In the postseason, Lester had a 2.51 ERA in 26 games (22 starts).
In the World Series, he was 4-1 with a 1.77 ERA in 35 2/3 innings.
The end nears
Lester pitched through some soreness in his final appearances and did not get a chance to add to that success with the Cardinals when they failed to advance past the wild-card game at Dodger Stadium.
Lester was positioned, if healthy, to be one of the team’s starters in the middle of a best-of-five National League Division Series. When Lester and Happ became free agents at season’s end, the Cardinals began their offseason shopping with an opening in their rotation. The Cardinals signed lefty Steven Matz. They did not pursue a reunion with Lester because, according to a source, they expected him to retire.
Lester said that was a possibility during his time with the Cardinals, pointing out how he was away from his family and chasing that 200th win while also not feeling he succeed in the same ways he had. Asked minutes after the clubhouse celebration what it meant to reach 200 wins before last season ended and the potential of retirement arrived, he spoke only about what he suddenly had lost.
“I’m kind of stuck for words,” he said.
Lester did open a window into his thinking about retirement in September, explaining how it was a discussion he had to to have with his family during the winter. He described how his children were getting older as his body was feeling older.
“The door is never shut, but you know I think at this point, where I’m at, physically and mentally, and all that stuff, it’s definitely something I need to sit down with my family at the end and decide not only what is best for me going forward, but what is best for my family going forward,” he said. “I’ve got some kids getting older now. I need to make some decisions for them as well.”